Phenylpyruvic acid → HCID 54518889, compound

HRID 2418404Notes

Reaction equation

HRID 2418404 reaction equation
[C:1]1([CH2:7][C:8](=O)[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15].C([BH3-])#N.[Na+]>CO.O>[C:9]([CH:8]([NH:13][C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 997Phenylpyruvic acidHCID 83525L-Alanyl-L-prolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 54518889HCID 54518889, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of phenylpyruvic acid (753 mg) and L-alanyl-L-proline (171 mg) in methanol-water are adjusted to pH 6.8 and treated with sodium cyanoborohydride (173 mg) at room temperature until reaction is complete. The product is absorbed on strong cation exchange resin and eluted with 2% pyridine in water to give 294 mg of crude diastereomeric product, N-(1-carboxy-2-phenylethyl)-L-alanyl-L-proline. A portion is purified by gel filtration (LH-20) for spectrographic analysis. The nmr spectrum shows a broad singlet at 7.2, complex absorption from 3.0 to 4.6, a multiplet at 2.1 and a pair of doublets at 1.5 ppm.

Workup

  1. customThe product is absorbed on strong cation exchange resin
  2. washeluted with 2% pyridine in water

Sources & evidence

ORD record
ord-2228e91051e64d46bdeccb199e83ecb2
Source dataset
uspto-grants-1984_09
Patent number
US04472380

Reaction notes

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